Dr. Kupersmith joined CCES in 2006 as Associate Headmaster, served as Headmaster beginning in 2008, first alongside Lee Cox who served as President, and then as the sole leader of the school as Headmaster from 2010 until June of 2020, making him the longest serving Headmaster in the school’s history. During Leonard’s tenure, he exhibited integrity, grit, wisdom, and great depth of character when making important and sometimes difficult decisions to steer CCES in pursuit of excellence. His engagement in the community was unmatched, and we are fortunate to have had a leader who championed CCES’s academics, athletics, the arts, and Episcopal values and traditions.
Through his leadership in the Faith in the Future campaign, the athletic department improved its athletic facilities through a new track, extending the Linda Reeves Field to make room for the new lacrosse program, producing a new tennis facility, converting the former tennis courts into practice fields, and constructing the Robertson-Navarro Baseball Pavilion. That same campaign created the Achievement Center and, of course, the Hartness Performing Arts Center, providing parity to the arts. All of these efforts raised CCES’s academic, athletic, and arts programs to levels unsurpassed by its peers.